3,3-bis(4-chlorobenzyl)-6-chloro-4-hydroxy-3,4-dihydro-1H-quinolin-2-one | 1614221-95-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 3,3-bis(4-chlorobenzyl)-6-chloro-4-hydroxy-3,4-dihydro-1H-quinolin-2-one
• 英文别名: 6-Chloro-3,3-bis[(4-chlorophenyl)methyl]-4-hydroxy-1,4-dihydroquinolin-2-one；6-chloro-3,3-bis[(4-chlorophenyl)methyl]-4-hydroxy-1,4-dihydroquinolin-2-one
• CAS: 1614221-95-2
• 化学式: C₂₃H₁₈Cl₃NO₂
• 分子量: 446.76
• InChiKey: GUCJAXXWMROWPV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2,4-喹啉二醇 在 sodium tetrahydroborate 、 potassium carbonate 作用下， 以 乙醇 、 水 、 乙酸乙酯 、 甲苯 为溶剂， 反应 48.0h， 生成 3,3-bis(4-chlorobenzyl)-6-chloro-4-hydroxy-3,4-dihydro-1H-quinolin-2-one
  参考文献：
  名称：

  Synthesis of symmetrically substituted 3,3-dibenzyl-4-hydroxy-3,4-dihydro-1H-quinolin-2-ones, as novel quinoline derivatives with antibacterial activity

  摘要：

  A novel series of symmetrically substituted 3,3-dibenzy1-4-hydroxy-3,4-dihydro-1H-quinolin-2-ones was synthesized and tested as antimicrobials. The minimum inhibitory concentration (MIC) values of the most active heterocycles were slightly higher than those exhibited by levofloxacin, employed as comparator. Structural factors affecting the activity were explored along three diversification points, including the substituents of the aromatic rings of the 3-benzyl moieties, as well as the functionalization of both, the homocyclic ring of the heterocycle and the quinolonic nitrogen atom. 6-Chloro and 3,3-bis(4'-chlorobenzyl) derivatives showed the lower MIC values. Optimally substituted heterocycles were synthesized, which exhibited enhanced activity. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.05.024

文献信息

• Synthesis of symmetrically substituted 3,3-dibenzyl-4-hydroxy-3,4-dihydro-1H-quinolin-2-ones, as novel quinoline derivatives with antibacterial activity
  作者：Matías D. Ferretti、Alexandre T. Neto、Ademir F. Morel、Teodoro S. Kaufman、Enrique L. Larghi

  DOI：10.1016/j.ejmech.2014.05.024

  日期：2014.6

  A novel series of symmetrically substituted 3,3-dibenzy1-4-hydroxy-3,4-dihydro-1H-quinolin-2-ones was synthesized and tested as antimicrobials. The minimum inhibitory concentration (MIC) values of the most active heterocycles were slightly higher than those exhibited by levofloxacin, employed as comparator. Structural factors affecting the activity were explored along three diversification points, including the substituents of the aromatic rings of the 3-benzyl moieties, as well as the functionalization of both, the homocyclic ring of the heterocycle and the quinolonic nitrogen atom. 6-Chloro and 3,3-bis(4'-chlorobenzyl) derivatives showed the lower MIC values. Optimally substituted heterocycles were synthesized, which exhibited enhanced activity. (C) 2014 Elsevier Masson SAS. All rights reserved.